Water → HCID 13499466, compound

HRID 1977438Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:18]=1)[C:12](OC)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].ClCCl.CO.O>CCOCC>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[CH:18]=1)[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 10 °C

Procedure

Methyl 3,5-di-tert-butyldimethylsilyloxybenzoate (170 g, 0.429 mole) was dissolved in ether (800 ml) and cooled to 10° C. Lithium aluminum hydride (14.2 g, 0.374 mole) was added in small portions. After 0.5 h TLC revealed complete conversion (dichloromethane:methanol 95:5), and water (20 ml) was added dropwise to destroy the excess of lithium aluminum hydride. Water/formic acid 4:1 (500 ml) was added to dissolve the aluminum salts, the organic layer was separated, and the aqueous layer was extracted with ether. The combined ether layers were washed with 0.4M sodium hydroxide, water, and brine. After drying (sodium sulfate), the ether was removed in vacuo to yield 147 g of the benzyl alcohol (0.399 mole, 93%).

Workup

customto destroy the excess of lithium aluminum hydride
additionWater/formic acid 4:1 (500 ml) was added
dissolutionto dissolve the aluminum salts
customthe organic layer was separated
extractionthe aqueous layer was extracted with ether
washThe combined ether layers were washed with 0.4M sodium hydroxide, water, and brine
dry with materialAfter drying (sodium sulfate)
customthe ether was removed in vacuo

Sources & evidence

ORD record: ord-1647ee0acab049baabbc48b12f57cc1f
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06232430B1

Reaction notes

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