[CH:1]1([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.CN1CCOCC1.C(OC(Cl)=O)C(C)C>O1CCCC1>[CH:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:15][CH:16]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]14-(Cyclohex-2-enyloxy)benzoic acid (25 g, 115 mmol) was dissolved in 250 mL dry tetrahydrofuran and cooled to -10° C. under an atmosphere of dry nitrogen. N-Methylmorpholine (12.6 mL, 115 mmol) and isobutylchloroformate (15.9 mL, 115 mmol) were added. After 10 minutes at -10° C. the mixture was warmed to room temperature and filtered. The volume was reduced to 50 mL under reduced pressure before cooling to 0° C. and adding diisobutylaluminum hydride (1.5M in toluene, 160 mL) over 10 minutes. After 30 minutes, the reaction was warmed to ambient temperature for 2 hours. The mixture was cooled in an ice bath, diluted with ether, quenched with methanol, and poured into cold Rochelle's salt solution. The crude product was extracted with ether, dried over Na2 SO4, and chromatographed eluting with 20% ethyl acetate in hexane to give 4.24 g (18%) of 4-(cyclohex-2-enyloxy)benzyl alcohol.
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