HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 363542Generated: October 30, 2026
tert-Butyldimethylsilyl chloride → Benzenemethanol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-
https://huagongshe.com/reaction/363542
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | Methyl 4-(hydroxymethyl)benzoate | HCID 81325 | — |
| Reactant | alpha-[(tert-Butyldimethylsilyloxymethyl)-benzyloxy][3-(tert-butyldimethylsilyloxymethyl)styrene] | HCID 21224724 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | alpha-Benzyloxy[3-(tert-butyldimethylsilyloxymethyl)styrene) | HCID 21253622 | — |
| Reactant | alpha-[4-(tert-Butyldimethylsilyloxymethyl)-benzyloxy][4-(tert-butyldimethylsilyloxymethyl)styrene] | HCID 21253626 | — |
| Product | Benzenemethanol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]- | HCID 10800836 | — |
Reaction Steps
α-[4-(tert-Butyldimethylsilyloxymethyl)-benzyloxy][4-(tert-butyldimethylsilyloxymethyl)styrene] and α-[(tert-Butyldimethylsilyloxymethyl )-benzyloxy][3-(tert-butyldimethylsilyloxymethyl)styrene]. (Formula II, R1 =tert-butyldimethylsilyloxymethylphenyl, R2 =4-tert-butyldimethylsilyloxymethylbenzyl). Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound uising Method C. 1H NMR (CCl4) δ 0.08 (12H, s), 0.91 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, s), 7.1-7.6 (8H, m); MS (CH4) 483 (M+ --CH3, 52%), 133 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05874511 |
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| Source dataset | uspto-grants-1999_02 |
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| ORD ID | ord-d2c46d9838e74d588022496c44a147a2 |
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| Source note | uspto-grants-1999_02 |
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