Hydrochloric Acid → HCID 54478410, compound

HRID 1742812Notes

Reaction equation

Cl.[C:2]([O:10][CH2:11][CH:12]1C[C:13]1([CH2:24][O:25][Si](C(C)(C)C)(C)C)[CH2:15][O:16][Si](C(C)(C)C)(C)C)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:33]O>>[CH3:33][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:2]([O:10][CH:11]1[CH2:12][C:13]1([CH2:15][OH:16])[CH2:24][OH:25])=[O:9]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 11798364HCID 11798364, compound

Product 1

HCID 54478410HCID 54478410, compoundYield 100%

Procedure

137 ml (137 mmol) of 1N hydrochloric acid, and 683 ml of methanol were added to 21.15 g (45.5 mmol) of 2,2-bis[(tert-butyldimethylsilyloxy)methyl]cyclopropylmethyl benzoate, and the solution was stirred for 40 minutes at room temperature. The solvent was distilled off, and the resulting oily product was purified by silica gel column chromatography (4% methanol/dichloromethane) to obtain 10.91 g (45.5 mmol, 100%) of 2,2-bis(hydroxymethyl)cyclopropyl methylbenzoate. This was a colorless oil; 1H-NMR (CDCl3) δ: 0.52 (dd, J=5.4, 5.4 Hz, 1H), 0.82 (dd, J=5.1, 8.7 Hz, 1H), 1.41 (m, 1H), 2.95 (broad s, 2H), 3.55 (d, J=11.4 Hz, 1H), 3.66 (d, J=11.4 Hz, 1H), 3.69 (d, J=12.0 Hz, 1H), 4.03 (d, J=12.0 Hz, 1H), 4.29 (dd, J= 8.7, 12.0 Hz, 1H), 4.57 (dd J=6.3, 12.0 Hz, 1H), 7.44 (m, 2H), 7.56 (m, 1H), 8.04 (m, 2H); FD MASS, M/z 236 (M+).

Workup

distillationThe solvent was distilled off
customthe resulting oily product was purified by silica gel column chromatography (4% methanol/dichloromethane)

Sources & evidence

ORD record: ord-a34c41389827438caced256257f5cd9d
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342840

Reaction notes

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